Condensed cyclic compound and organic light-emitting device including the same

ABSTRACT

A condensed cyclic compound represented by Formula 1: 
     
       
         
         
             
             
         
       
         
         
           
             wherein, in Formula 1, X 1  to X 8 , X 11  to X 18 , Y 11 , and Z 11  to Z 14  are the same as described in the specification.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2015-0105302, filed on Jul. 24, 2015, in the KoreanIntellectual Property Office, the content of which is incorporatedherein in its entirety by reference.

BACKGROUND

1. Field

The present disclosure relates to condensed cyclic compounds and organiclight-emitting devices including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices thathave wide viewing angles, high contrast ratios, short response times. Inaddition, OLEDs display excellent luminance, driving voltage, andresponse speed characteristics, and produce full-color images.

In an example, an organic light-emitting device includes an anode, acathode, and an organic layer that is disposed between the anode and thecathode and includes an emission layer. A hole transport region may bedisposed between the anode and the emission layer, and an electrontransport region may be disposed between the emission layer and thecathode. Holes provided from the anode may move toward the emissionlayer through the hole transport region, and electrons provided from thecathode may move toward the emission layer through the electrontransport region. Carriers, such as holes and electrons, recombine inthe emission layer to produce excitons. These excitons change from anexcited state to a ground state, thereby generating light.

Different types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

One or more embodiments relate to a novel condensed cyclic compound andan organic light-emitting device including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented exemplary embodiments.

Provided is condensed cyclic compounds represented by Formula 1:

In Formula 1,

X₁ is N or C(R₁), X₂ is N or O(R₂), X₃ is N or C(R₃), X₄ is N or C(R₄),X₅ is N or C(R₅), X₆ is N or C(R₆), X₇ is N or C(R₇), X₈ is N or C(R₈),X₁₁ is N or C(R₁₁), X₁₂ is N or C(R₁₂), X₁₃ is N or C(R₁₃), X₁₄ is N orC(R₁₄), X₁₅ is N or C(R₁₅), X₁₅ is N or C(R₁₆), X₁₇ is N or C(R₁₇), andX₁₈ is N or C(R₁₈),

Y₁₁ is O, S, C(R₁₀₁)(R₁₀₂), or Si(R₁₀₁)(R₁₀₂);

Z₁₁ to Z₁₄ are each independently selected from N, C(A₁₁), andC(A_(l2)); and at least one selected from Z₁₁ to Z₁₄ is C(A₁₁);

A₁₁ includes at least one cyano group (CN); and may be a cyano group(CN) or a group represented by one of Formulae 2-1 to 2-10;

A₁₂ is selected from a hydrogen, a deuterium, —F, a hydroxyl group, acyano group (CN), a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, a hydroxyl group, a cyano group(CN), a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, and a phosphoric acid group or asalt thereof;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group, each substituted with at least oneselected from a deuterium, —F, a hydroxyl group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a pyridinyl group, afluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and—Si(Q₂₁)(Q₂₂)(Q₂₃); and

—Si(Q₃₁)(Q₃₂)(Q₃₃);

In Formulae 2-1 to 2-10,

X₂₁ is N or O(R₂₁), X₂₂ is N or C(R₂₂), X₂₃ is N or C(R₂₃), X₂₄ is N orC(R₂₄), and X₂₅ is N or O(R₂₅),

R₁ to R₈, R₁₁ to R₁₈, R₁₀₁, R₁₀₂, R₂₁ to R₂₅, and R₂₀₁ to R₂₀₃ are eachindependently selected from

a hydrogen, a deuterium, —F, a hydroxyl group, a cyano group (CN), anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, a hydroxyl group, a cyano group(CN), a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, and a phosphoric acid group or asalt thereof;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group, each substituted with at least oneselected from a deuterium, —F, a hydroxyl group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a pyridinyl group, afluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group and—Si(Q₁)(Q₂)(Q₃); and

—Si(Q₁₁)(Q₁₂)(Q₁₃),

R₁₀₁ and R₁₀₂ may be optionally linked to each other to form a saturatedring or an unsaturated ring;

b201 is selected from 1, 2, 3, 4, and 5;

b202 and b203 are each independently selected from 1, 2, 3, and 4; and

* indicates a carbon atom in Formula 1,

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are eachindependently selected from a hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, afluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

Provided is an organic light-emitting device including: a firstelectrode; a second electrode; and an organic layer between the firstelectrode and the second electrode, the organic layer including anemission layer and at least one of condensed cyclic compoundsrepresented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the exemplary embodiments,taken in conjunction with the accompanying drawings in which:

FIG. 1 is a schematic view of an organic light-emitting device accordingto an embodiment;

FIG. 2 is a graph of efficiency (candelas per ampere (cd/A) versusluminance (candelas per square meter), which is luminance-efficiencygraph of organic light-emitting devices manufactured according toExample 1 and Comparative Examples 1 to 4;

FIG. 3 is a graph of external quantum efficiency (percent, %) versusluminance (candelas per square meter), which is a luminance-externalquantum efficiency graph of the organic light-emitting devicesmanufactured according to Example 1 and Comparative Examples 1 to 4; and

FIG. 4 is a graph of intensity (arbitrary unit) versus wavelength(nanometer, nm) showing electroluminescent (EL) spectra of the organiclight-emitting devices manufactured according to Example 1 andComparative Examples 1 to 4.

DETAILED DESCRIPTION

Reference will now be made in detail to exemplary embodiments, examplesof which are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present exemplary embodiments may have different forms and shouldnot be construed as being limited to the descriptions set forth herein.Accordingly, the exemplary embodiments are merely described below, byreferring to the figures, to explain aspects. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims. In the drawings, likereference numerals denote like elements throughout, and thus redundantdescription thereof will be omitted.

It will be understood that, although the terms first, second, third etc,may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” As used herein, the terms such as“comprising”, “including”, “having”, or the like are intended toindicate the existence of the features regions, integers, steps,operations, components, and/or elements disclosed in the specification,and are not intended to preclude the possibility that one or more otherfeatures or elements may exist or may be added.

It will also be understood that when an element such as a layer, aregion or a component is referred to as being “on” another layer orelement, it can be directly on the other layer or element, orintervening layers, regions, or components may also be present. Incontrast, when an element is referred to as being “directly on” anotherelement, there are no intervening elements present.

In the drawings, the sizes of elements are exaggerated or reduced forease of description. The size or thickness of each element shown in thedrawings are arbitrarily illustrated for better understanding or ease ofdescription, and thus the present disclosure is not limited thereto.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

A condensed cyclic compound according to an embodiment is represented byFormula 1:

In Formula 1, X₁ may be N or C(R₁), X₂ may be N or C(R₂), X₃ may be N orC(R₃), X₄ may be N or C(R₄), X₅ may be N or C(R₅), X₆ may be N or C(R₆),X₇ may be N or C(R₇), X₈ may be N or C(R₈), X₁₁ may be N or C(R₁₁), X₁₂may be N or C(R₁₂), X₁₃ may be N or C(R₁₃), X₁₄ may be N or C(R₁₄), X₁₅may be N or C(R₁₅), X₁₆ may be N or C(R₁₆), X₁₇ may be N or C(R₁₇), andX₁₈ may be N or C(R₁₈).

For example, in Formula 1, X₁ may be N, X₂ may be C(R₂), X₃ may beC(R₃), X₄ may be C(R₄), X₅ may be C(R₅), X₆ may be C(R₆), X₇ may beC(R₇), X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may beC(R₁₃), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R16), X₁₇ maybe C(R₁₇), and X₁₈ may be C(R₁₈), but they are not limited thereto.

For example, in Formula 1, X₁ may be C(R₁), X₂ may be N, X₃ may beC(R₃), X₄ may be C(R₄), X₅ may be C(R₅), X₆ may be C(R₆), X₇ may beC(R₇), X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may beC(R₁₃), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R₁₆), X₁₇ maybe C(R₁₇), and X₁₈ may be C(R₁₈), but they are not limited thereto.

For example, in Formula 1, X₁ may be C(R₁), X₂ may be C(R₂), X₃ may beN, X₄ may be C(R₄), X₅ may be C(R₅), X₆ may be C(R₆), X₇ may be C(R₇),X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may beC(R₁₃), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R₁₆), X₁₇ maybe C(R₁₇), and X₁₈ may be C(R₁₈), but they are not limited thereto.

For example, in Formula 1, X₁ may be C(R₁), X₂ may be C(R₂), X₃ may beC(R₃), X₄ may be N, X₅ may be C(R₅), X₆ may be C(R₆), X₇ may be C(R₇),X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may beC(R₁₃), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R₁₆), X₁₇ maybe C(R₁₇), and X₁₈ may be C(R₁₈), but they are not limited thereto.

For example, in Formula 1, X₁ may be C(R₁), X₂ may be C(R₂), X₃ may beC(R₃), X₄ may be C(R₄), X₅ may be N, X₆ may be C(R₆), X₇ may be C(R₇),X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may beC(R₁₃), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R₁₆), X₁₇ maybe C(R₁₇), and X₁₈ may be C(R₁₈), but they are not limited thereto.

For example, in Formula 1, X₁ may be C(R₁), X₂ may be C(R₂), X₃ may beC(R₃), X₄ may be C(R₄), X₅ may be C(R₅), X₆ may be N, X₇ may be C(R₇),X₈ may be C(R₆), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may beC(R₁₃), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R₁₆), X₁₇ maybe C(R₁₇), and X₁₈ may be C(R₁₈), but they are not limited thereto.

For example, in Formula 1, X₁ may be C(R₁), X₂ may be C(R₂), X₃ may beC(R₃), X₄ may be C(R₄), X₅ may be C(R₅), X₆ may be C(R₆), X₇ may be N,X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may beC(R₁₃), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R₁₆), X₁₇ maybe C(R₁₇), and X₁₈ may be C(R₁₈), but they are not limited thereto.

For example, in Formula 1, X₁ may be C(R₁), X₂ may be C(R₂), X₃ may beC(R₃), X₄ may be C(R₄), X₅ may be C(R₅), X₆ may be C(R₆), X₇ may beC(R₇), X₈ may be N, X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may beC(R₁₃), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R₁₆), X₁₇ maybe C(R₁₇), and X₁₈ may be C(R₁₈), but they are not limited thereto.

For example, in Formula 1, X₁ may be C(R₁), X₂ may be C(R₂), X₃ may beC(R₃), X₄ may be C(R₄), X₅ may be C(R₅), X₆ may be C(R₆), X₇ may beC(R₇), X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may beC(R₁₃), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R₁₆), X₁₇ maybe C(R₁₇), and X₁₈ may be C(R₁₈), but they are not limited thereto.

In Formula 1, Y₁₁ may be O, S, C(R₁₀₁)(R₁₀₂), or Si(R₁₀₁)(R₁₀₂). R₁₀₁and R₁₀₂ will be explained in detail below,

For example, in Formula 1, Y₁₁ may be C(R₁₀₁)(R₁₀₂), but is not limitedthereto,

In Formula 1, Z₁₁ to Z₁₄ may be each independently selected from N,C(A₁₁), and C(A₁₂); and at least one of Z₁₁ to Z₁₄ may be C(A₁₁), A₁₁and A₁₂ will be explained in detail below.

For example, in Formula 1, Z₁₁ may be N, Z₁₂ may be C(A_(l2)), Z₁₃ maybe C(A₁₁), and Z₁₄ may be C(A₁₂), but they are not limited thereto.

For example, in Formula 1, Z₁₁ may be C(A₁₂), Z₁₂ may be N, Z₁₃ may beC(A₁₁), and Z₁₄ may be C(A₁₂), but they are not limited thereto.

For example, in Formula 1, may be C(A_(l2)), Z₁₂ may be C(A₁₂), Z₁₃ maybe C(A₁₁), and Z₁₄ may be N, but they are not limited thereto.

For example, in Formula 1, Z₁₁ may be C(A₁₂), Z₁₂ may be C(A_(l2)), Z₁₃may be C(A₁₁), and Z₁₄ may be C(A₁₂), but they are not limited thereto.

In some embodiments, in Formula 1, Z₁₁ may be N, Z₁₂ may be CH, Z₁₃ maybe C(A₁₁), and Z₁₄ may be CH, but they are not limited thereto.

In some embodiments, in Formula 1, Z₁₁ may be CH, Z₁₂ may be N, Z₁₃ maybe C(A₁₁), and Z₁₄ may be CH, but they are not limited thereto.

In some embodiments, in Formula 1, Z₁₁ may be CH, Z₁₂ may be CH, Z₁₃ maybe C(A₁₁), and Z₁₄ may be N, but they are not limited thereto.

In some embodiments, in Formula 1, Z₁₁ may be CH, Z₁₂ may be CH, Z₁₃ maybe C(A₁₁), and Z₁₄ may be CH, but they are not limited thereto.

In Formula 1, A₁₁ includes at least one cyano group (CN); and may be acyano group (CN) or a group represented by one of Formulae 2-1 to 2-10:

In Formulae 2-1 to 2-10,

* indicates a carbon atom in Formula 1;

X₂₁ may be N or C(R₂₁), X₂₂ may be N or C(R₂₂) X₂₃ may be N or C(R₂₃),X₂₄ may be N or C(R₇₄), and X₂₅ may be N or C(R₂₅), and

R₂₁ to R₂₅, R₂₀₁ to R₂₀₃, and b201 to b203 will be explained in detailbelow.

For example, A₁₁ in Formula 1 may be a cyano group (CN), or may berepresented by one of Formulae 2-1 to 2-7, but is not limited thereto.

In some embodiments, A₁₁ in Formula 1 may be represented by one ofFormulae 2-2, 2-5, and 2-8; and

in Formulae 2-2, 2-5, and 2-8,

X₂₂ may be N, X₂₃ may be C(R₂₃), X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₂ may be C(R₂₂), X₂₃ may be N, X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₂ may be C(R₂₂), X₂₃ may be C(R₂₃), X₂₄ may be N, and X₂₅ may beC(R₂₅); or

X₂₂ may be C(R₂₂), X₂₃ may be C(R₂₃), X₂₄ may be C(R₂₄), and X₂₅ may beN, but they are not limited thereto.

In some embodiments, A₁₁ in Formula 1 may be represented by one ofFormulae 2-3, 2-6 and 2-9; and

in Formulae 2-3, 2-6, and 2-9,

X₂₁ may be N, X₂₃ may be C(R₂₃), X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₁ may be C(R₂₁), X₂₃ may be N, X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₁ may be C(R₂₁), X₂₃ may be C(R₂₃), X₂₄ may be N, and X₂₅ may beC(R₂₅); or

X₂₁ may be C(R₂₁), X₂₃ may be C(R₂₃), X₂₄ may be C(R₂₄), and X₂₅ may beN, but they are not limited thereto.

In some embodiments, A₁₁ in Formula 1 may be represented by one ofFormulae 2-4₇ 2-7, and 2-10; and

in Formulae 2-4, 2-7 and 2-10,

X₂₁ may be N, X₂₂ may be C(R₂₂), X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₁ may be C(R₂₁), X₂₂ may be N, X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₁ may be C(R₂₁), X₂₂ may be C(R₂₂), X₂₄ may be N, and X₂₅ may beC(R₂₅); or

X₂₁ may be C(R₂₁), X₂₂ may be C(R₂₂), X₂₄ may be C(R₂₄), and X₂₅ may beN, but they are not limited thereto.

In some embodiments, A₁₁ in Formula 1 may be a cyano group (CN) or agroup represented by one of Formulae 3-1 to 3-110, but is not limitedthereto:

In Formulae 3-1 to 3-110,

* indicates a carbon atom in Formula 1;

X₂₁ may be N or C(R₂₁), X₂₂ may be N or C(R₂₂), X₂₃ may be N or C(R₂₃),X₂₄ may be N or C(R₂₄), and X₂₅ may be N or C(R₂₅), and

R₂₁ to R₂₅, R₂₀₂, R₂₀₃, b202, and b203 will be explained in detailbelow.

In some embodiments, in Formulae 3-12 to 3-22, 3-45 to 3-55, and 3-78 to3-88,

X₂₂ may be N, X₂₃ may be C(R₂₃), X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₂ may be C(R₂₂), X₂₃ may be N, X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₂ may be C(R₂₂), X₂₃ may be C(R₂₃), X₂₄ may be N, and X₂₅ may beC(R₂₅); or

X₂₂ may be C(R₂₂), X₂₃ may be C(R₂₃), X₂₄ may be C(R₂₄), and X₂₅ may beN, but they are not limited thereto.

In some embodiments, in Formulae 3-23 to 3-33, 3-56 to 3-66, and 3-89 to3-99,

X₂₁ may be N, X₂₃ may be C(R₂₃), X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₁ may be C(R₂₁), X₂₃ may be N, X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₁ may be C(R₂₁), X₂₃ may be C(R₂₃), X₂₄ may be N, and X₂₅ may beC(R₂₅); or

X₂₁ may be C(R₂₁), X₂₃ may be C(R₂₃), X₂₄ may be C(R₂₄), and X₂₅ may beN, but they are not limited thereto.

In some embodiments, in Formulae 3-34 to 3-44, 3-67 to 3-77, and 3-100to 3-110,

X₂₁ may be N, X₂₂ may be C(R₂₂), X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₁ may be C(R₂₁), X₂₂ may be N, X₂₄ may be C(R₂₄), and X₂₅ may beC(R₂₅);

X₂₁ may be C(R₂₁), X₂₂ may be C(R₂₂), X₂₄ may be N, and X₂₅ may beC(R₂₅); or

X₂₁ may be C(R₂₁), X₂₂ may be C(R₂₂), X₂₄ may be C(R₂₄), and X₂₅ may beN, but they are not limited thereto.

In some embodiments, A₁₁ in Formula 1 may be a cyano group (CN) or agroup represented by one of Formulae 4-1 to 4-110, but the structurethereof is not limited thereto:

In Formulae 4-1 to 4-110,

* indicates a carbon atom in Formula 1; and

R₂₀₂, R₂₀₃, b201, and b202 will be explained in detail belo

In Formula 1, A₁₂ may be selected from hydrogen, deuterium, —F, ahydroxyl group, a cyano group (CN), a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, and aC₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, a hydroxyl group, a cyano group(CN), a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, and a phosphoric acid group or asalt thereof;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group, each substituted with at least oneselected from a deuterium, —F, a hydroxyl group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a pyridinyl group, afluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and—Si(Q₂₁)(Q₂₂)(Q₂₃); and

—Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₂₁ to Q₂₃ and Q₃₁ to Q₃₃ may be each independently selectedfrom hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a pyridinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group.

For example, A₁₂ in Formula 1 may be selected from hydrogen, deuterium,—F, a hydroxyl group, a cyano group (CN), a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, and aC₁-C₂₀ alkoxy group;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group; and

—Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₃₁ to Q₃₃ may be each independently selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group,and a pyridinyl group, but A₁₂ is not limited thereto.

R₁ to R₈, R₁₁ to R₁₈, R₁₀₁, R₁₀₂, R₂₁ to R₂₅, R₂₀₁ to R₂₀₃ in Formulae 1and 2-1 to 2-10 may be each independently selected from

hydrogen, deuterium, —F, a hydroxyl group, a cyano group (CN), a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, a hydroxyl group, a cyano group(CN), a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, and a phosphoric acid group or asalt thereof;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup and a dibenzothiophenyl group, each substituted with at least oneselected from a deuterium, —F, a hydroxyl group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a pyridinyl group, afluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and—Si(Q₁)(Q₂)(Q₃);

—Si(Q₁₁)(Q₁₂)(Q₁₃); and

R₁₀₁ and R₁₀₂ may be optionally linked to each other to form a saturatedring or an unsaturated ring,

wherein Q₁ to Q₃ and Q₁₁ to Q₁₃ may be each independently selected fromhydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group.

For example, R₁ to R₈, R₁₁ to R₁₈, R₁₀₁, R₁₀₂, R₂₁ to R₂₅, and R₂₀₁ toR₂₀₃ in Formulae 1 and 2-1 to 2-10 may be each independently selectedfrom

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an isopentyl group, a sec-pentyl group, atert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexylgroup, a tert-hexyl group, an n-heptyl group, an isoheptyl group, asec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctylgroup, a sec-octyl group, a tert-octyl group, an n-nonyl group, anisononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group,an isodecyl group, a sec-decyl group, a tert-decyl group, a methoxygroup, an ethoxy group, a propoxy group, a butoxy group, a pentoxygroup, a phenyl group, a pyridinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an isopentyl group, a sec-pentyl group, atert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexylgroup, a tert-hexyl group, an n-heptyl group, an isoheptyl group, asec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctylgroup, a sec-octyl group, a tert-octyl group, an n-nonyl group, anisononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group,an isodecyl group, a sec-decyl group, a tert-decyl group, a methoxygroup, an ethoxy group, a propoxy group, a butoxy group, a pentoxygroup, a phenyl group, a pyridinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof; and

—Si(Q₁₁)(Q₁₂)(Q₁₃),

wherein Q₁₁ to Q₁₃ may be each independently selected from hydrogen, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, anda dibenzothiophenyl group, but they are not limited thereto,

In some embodiments, R₁ to R₈, R₁₁ to R₁₈, R₂₁ to R₂₅, and R₂₀₁ to R₂₀₃in Formulae 1 and 2-1 to 2-10 may be each independently selected from

hydrogen, deuterium, a cyano group, a methyl group, an ethyl group, ann-propyl group, an isopropyl group, an n-butyl group, an isobutyl group,a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentylgroup, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, anisohexyl group, a sec-hexyl group, a tert-hexyl group, and—Si(Q₁₁)(Q₁₂)(Q₁₃),

wherein Q₁₁ to Q₁₃ may be each independently selected from hydrogen, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, and a phenyl group, but theyare not limited thereto.

In some embodiments, R₁₀₁ and R₁₀₂ in Formula 1 may be linked to eachother to form the structure represented by Formula 8, but they are notlimited thereto:

In Formula 8,

* indicates a carbon atom that belongs to Y₁₁ in Formula 1;

X₈₁ may be N or C(R₈₁), X₈₂ may be N or C(R₈₂), X₈₃ may be N or C(R₈₃),X₈₄ may be N or C(R₈₄), X₈₅ may be N or O(R₈₅), X₈₆ may be N or C(R₈₆),X₈₇ may be N or C(R₈₇), and X₈₈ may be N or C(R₈₈), and

R₈₁ to R₈₈ may be each independently selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₃₁ to Q₃₃ may be each independently selected from hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, and a triazinyl group.

In some embodiments, R₁₀₁ and R₁₀₂ in Formula 1 may be linked to eachother to form the structure represented by Formula 9, but they are notlimited thereto:

In Formula 9,

* indicates a carbon atom that belongs to Y₁₁ in Formula 1; and

R₈₁ to R₈₈ may be each independently selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₃₁ to Q₃₃ may be each independently selected from hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, and a triazinyl group.

In some embodiments, R₁₀₁ and R₁₀₂ in Formula 1 may be linked to eachother to form the structure represented by one of Formulae 10-1 and10-2, but they are not limited thereto:

In Formula 10-1 and 10-2,

* indicates a carbon atom that belongs to Y₁₁ in Formula 1; and

R₈₁ to R₈₈ may be each independently selected from hydrogen; deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₃₁ to Q₃₃ are each independently selected from hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, and a triazinyl group.

In Formulae 2-1 to 2-10, b201 indicates the number of groups R₂₀₁, andb201 may be selected from 1, 2, 3, 4, and 5. When b201 is 2 or more,groups R₃₀₁ may be identical to or different from each other.

In Formulae 2-1 to 2-10, b202 indicates the number of groups R₂₀₂, andb202 may be selected from 1, 2, 3, and 4. When b202 is 2 or more, groupsR₂₀₂ may be identical to or different from each other.

In Formulae 2-1 to 2-10, b203 indicates the number of groups R₂₀₃, andb203 may be selected from 1, 2, 3, and 4. When b203 is 2 or more, groupsR₂₀₃ may be identical to or different from each other.

For example, at least one selected from X₃, X₆, X₁₃, and X₁₆ in Formula1 may be C(CN), but embodiments are not limited thereto.

In some embodiments, R₁, R₂, R₄, R₅, R₇, R₈, R₁₁, R₁₂, R₁₄, R₁₅, R₁₇,and R₁₈ in Formula 1 may not be a cyano group, but they are not limitedthereto.

The condensed cyclic compound represented by Formula 1 may berepresented by one of Formulae 1-1 and 1-2, but they are not limitedthereto;

In Formulae 1-1 and 1-2,

X₁ to X_(8,) X₁₁ to X₁₈, Y₁₁, and A₁₁ may be understood by referring todescriptions thereof made in connection with Formula 1;

A_(12a), A_(12b), and A_(12c) may be understood by referring todescriptions thereof made in connection with A_(l2) in Formula 1.

For example, A₁₁ in Formulae 1-1 and 1-2 may be a cyano group (CN), or agroup represented by one of Formulae 4-1 to 4-110, but A₁₁ is notlimited thereto.

In some embodiments, at least one selected from X₃, X₈, X₁₃, and X₁₆ inFormulae 1-1 and 1-2 may be C(CN), but embodiments are not limitedthereto.

The condensed cyclic compound represented by Formula 1 may berepresented by one of Formulae 1-3 to 1-6, but they are not limitedthereto:

In Formulae 1-3 to 1-6,

X₁ to X₈, X₁₁ to X₁₈, Y₁₁, R₁₀₁, R₁₀₂, and A₁₁ may be understood byreferring to descriptions thereof made in connection with Formula 1;

A_(12a), A_(12b), and A_(12c) may be understood by referring todescriptions thereof made in connection with A₁₂ in Formula 1;

R₈₁ to R₈₈ may be each independently selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃);

Q₃₁ to Q₃₃ may be each independently selected from hydrogen, a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, and a triazinyl group.

For example, A₁₁ in Formulae 1-3 to 1-6 may be a cyano group (CN) or agroup represented by any one of Formulae 4-1 to 4-110, but is notlimited thereto.

In some embodiments, at least one of X₃, X₆, X₁₃, and X₁₆ in Formulae1-3 to 1-6 may be C(CN), but embodiments are not limited thereto.

The condensed cyclic compound represented by Formula 1 may be selectedfrom one of Formulae 1-11 to 1-25, but embodiments are not limitedthereto:

In Formulae 1-11 to 1-25,

X₁, X₂, X₄, X₅, X₇, X₈, X₁₁, X₁₂, X₁₄, X₁₅, X₁₇, X₁₈, Y₁₁, and Z₁₁ toZ₁₄ may be understood by referring to descriptions thereof made inconnection with Formula 1.

For example, in Formulae 1-11 to 1-25, X₁ may be N, X₂ may be C(R₂), X₄may be C(R₄), X₅ may be C(R₅), X₇ may be C(R₇), X₈ may be C(R₈), X₁₁ maybe C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₇may be C(R₁₇), and X₁₈ may be C(R₁₈);

X₁ may be C(R₁), X₂ may be N, X₄ may be C(R₄), X₅ may be C(R₅), X₇ maybe C(R₇), X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈);

X₁ may be C(R₁), X₂ may be C(R₂), X₄ may be N, X₅ may be C(R₅), X₇ maybe C(R₇), X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈);

X₁ may be C(R₁), X₂ may be C(R₂), X₄ may be C(R₄), X₅ may be N, X₇ maybe C(R₇), X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈);

X₁ may be C(R₁), X₂ may be C(R₂), X₄ may be C(R₄), X₅ may be C(R₅), X₇may be N, X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈);or

X₁ may be C(R₁), X₂ may be C(R₂), X₄ may be C(R₄), X₅ may be C(R₅), X₇may be C(R₇), X₈ may be N, X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₈), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈),but they are not limited thereto.

In some embodiments, Z₁₁ to Z₁₄ in Formulae 1-11 to 1-25 may be eachindependently selected from N, C(A₁₁), and C(A_(l2)); and at least oneof Z₁₁ to Z₁₄ is C(A₁₁); and

A₁₁ includes at least one cyano group (CN), and may be a cyano group(CN) or a group represented by one of Formulae 4-1 to 4-90, but they arenot limited thereto.

In some embodiments, in Formulae 1-11 to 1-25, Z₁₁ may be N, Z₁₂ may beC(A_(l2)), Z₁₃ may be C(A₁₁), and Z₁₄ may be C(A₁₂);

Z₁₁ may be C(A₁₂), Z₁₂ may be N, Z₁₃ may be C(A₁₁), and Z₁₄ may beC(A₁₂);

Z₁₁ may be C(A₁₂), Z₁₂ may be C(A₁₂), Z₁₃ may be C(A₁₁), and Z₁₄ may beN; or

Z₁₁ may be C(A₁₂), Z₁₂ may be C(A₁₂), Z₁₃ may be C(A₁₁), and Z₁₄ may beC(A₁₂), but they are not limited thereto.

The condensed cyclic compound represented by Formula 1 may berepresented by one of Formulae 1-31 to 1-45, but is not limited thereto:

In Formulae 1-31 to 1-45,

X₁, X₂, X₄, X₅, X₇, X₈, X₁₁, X₁₂, X₁₄, X₁₅, X₁₇, X₁₈, and Z₁₁ to Z₁₄ maybe understood by referring to descriptions thereof made in connectionwith Formula 1; and

R₈₁ to R₈₈ may be each independently selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₃₁ to Q₃₃ may be each independently selected from hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, and a triazinyl group.

For example, in Formulae 1-31 to 1-45, X₁ may be N, X₂ may be C(R₂), X₄may be C(R₄), X₅ may be C(R₅), X₇ may be C(R₇), X₈ may be C(R₈), X₁₁ maybe C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₇may be C(R₁₇), and X₁₈ may be C(R₁₈);

X₁ may be C(R₁), X₂ may be N, X₄ may be C(R₄), X₅ may be C(R₅), X₇ maybe C(R₇), X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈);

X₁ may be C(R₁), X₂ may be C(R₂), X₄ may be N, X₅ may be C(R₅), X₇ maybe C(R₇), X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈);

X₁ may be C(R₁), X₂ may be C(R₂), X₄ may be C(R₄), X₅ may be N, X₇ maybe C(R₇), X₈ may be C(R₈), X₁₁ may be C(R11), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈);

X₁ may be C(R₁), X₂ may be C(R₂), X₄ may be C(R₄), X₅ may be C(R₅), X₇may be N, X₈ may be C(R₈), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈);or

X₁ may be C(R₁), X₂ may be C(R₂), X₄ may be C(R₄), X₅ may be C(R₅), X₇may be C(R₇), X₈ may be N, X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅), X₁₇ may be C(R₁₇), and X₁₈ may be C(R₁₈),but they are not limited thereto.

In some embodiments, Z₁₁ to Z₁₄ in Formulae 1-31 to 1-45 may be eachindependently selected from N, C(A₁₁), and C(A₁₂); and at least one ofZ₁₁ to Z₁₄ may be C(A₁₁); and

A_(ll) includes at least one cyano group (CN), and may be a cyano group(CN) or a group represented by one of Formulae 4-1 to 4-110, but A₁₁ isnot limited thereto.

The condensed cyclic compound represented by Formula 1 may berepresented by one of Formulae 1-51 to 1-59 and 1-61 to 1-69, but is notlimited thereto:

In Formulae 1-51 to 1-59 and 1-61 to 1-69,

X₁, X₂, X₄, X₅, X₇, X₈, X₁₁, X₁₂, X₁₄, X₁₅, X₁₇, X₁₈, Y₁₁, and A₁₁ maybe understood by referring to descriptions thereof made in connectionwith Formula 1.

The condensed cyclic compound represented by Formula 1 may berepresented by one of Formulae 1-71 to 1-79 and 1-81 to 1-89, but is notlimited thereto:

In Formulae 1-71 to 1-79 and 1-81 to 1-89,

X₁, X₂, X₄, X₅, X₇, X₈, X₁₁, X₁₂, X₁₄, X₁₅, X₁₇, X₁₈, and A₁₁ may beunderstood by referring to descriptions thereof made in connection withFormula 1; and

R₈₁ to R₈₈ may be each independently selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₃₁ to Q₃₃ may be each independently selected from hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, and a triazinyl group.

The condensed cyclic compound represented by Formula 1 may be selectedfrom Compounds 1 to 134, but is not limited thereto:

The condensed cyclic compound represented by Formula 1 necessarilyincludes A₁₁ having at least one cyano group, and accordingly, thethermal stability and electric characteristics thereof may be improved.Accordingly, an organic light-emitting device including the condensedcyclic compound represented by Formula 1 may have an improved lifespanand improved efficiency.

A highest occupied molecular orbita (HOMO) energy level and a lowestunoccupied molecular orbital (LUMO) energy level of the condensed cycliccompound represented by Formula 1 may be adjustable by changing thenumber of cyano groups included therein, and hole or electron mobilityof the condensed cyclic compound represented by Formula 1 may beadjustable by changing the number of phenyl groups included in thecondensed cyclic compound included therein.

Synthesis methods for the condensed cyclic compound represented byFormula 1 may be recognizable to one of ordinary skill in the art byreferring to the following Synthesis Examples.

The condensed cyclic compound represented by Formula 1 is suitable foruse in an organic layer of an organic light-emitting device, forexample, a host constituting an emission layer included in the organiclayer. Accordingly, another aspect provides an organic light-emittingdevice including:

a first electrode;

a second electrode; and

an organic layer between the first electrode and the second electrode,

wherein the organic layer includes an emission layer and the condensedcyclic compound represented by Formula 1.

The organic light-emitting device may have, due to the inclusion of anorganic layer including the condensed cyclic compound represented byFormula 1, low driving voltage, high efficiency, high luminance, highquantum emission efficiency, and a long lifespan.

The condensed cyclic compound of Formula 1 may be used between a pair ofelectrodes of an organic light-emitting device. For example, thecondensed cyclic compound represented by Formula 1 may be included inthe emission layer. The condensed cyclic compound may act as a host, andin this case, the emission layer may further include a dopant.

The expression that “(an organic layer) includes a condensed cycliccompound” used herein may include an embodiment in which “(an organiclayer) includes identical compounds represented by Formula 1 and anembodiment in which (an organic layer) includes two or more differentcondensed cyclic compounds represented by Formula 1.

For example, the organic layer may include, as the condensed cycliccompound, only Compound 1, In this regard, Compound 1 may exist in anemission layer of the organic light-emitting device. In someembodiments, the organic layer may include, as the condensed cycliccompound, Compound 1 and Compound 2. In this regard, Compound 1 andCompound 2 may be included in an identical layer (for example, Compound1 and Compound 2 all may be included in an emission layer).

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode; or the first electrode may be a cathode,which is an electron injection electrode, or the second electrode may bean anode, which is a hole injection electrode.

For example, the first electrode may be an anode, and the secondelectrode may be a cathode, and the organic layer may include:

i) a hole transport region that is disposed between the first electrodeand the emission layer, wherein the hole transport region may include atleast one selected from a hole injection layer, a hole transport layer,and an electron blocking layer, and

ii) an electron transport region that is disposed between the emissionlayer and the second electrode, wherein the electron transport regionmay include at least one selected from a hole blocking layer, anelectron transport layer, and an electron injection layer.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers between the first electrode and the secondelectrode of the organic light-emitting device. The “organic layer” mayinclude, in addition to an organic compound, an organometallic complexincluding metal.

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. Hereinafter, the structure of an organiclight-emitting device according to an embodiment and a method ofmanufacturing an organic light-emitting device according to anembodiment will be described in connection with FIG. 1. The organiclight-emitting device 10 includes a first electrode 11, an organic layer15, and a second electrode 19, which are sequentially stacked in thisorder.

A substrate may be additionally disposed under the first electrode 11 orabove the second electrode 19. For use as the substrate, any substratethat is used in general organic light-emitting devices may be used, andthe substrate may be a glass substrate or transparent plastic substrate,each with excellent mechanical strength, thermal stability,transparency, surface smoothness, ease of handling, andwater-resistance.

The first electrode 11 may be formed by depositing or sputtering amaterial for forming a first electrode on the substrate. The firstelectrode 11 may be an anode. The material for the first electrode 11may be selected from materials with a high work function to facilitatehole injection. The first electrode 11 may be a reflective electrode ora transmissive electrode. The material for the first electrode 11 may beindium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), orzinc oxide (ZnO). In some embodiments, the material for the firstelectrode 11 may be metal, such as magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layer structure or amulti-layer structure including two or more layers. For example, thefirst electrode 11 may have a three-layered structure of ITO/Ag/ITO, butthe structure of the first electrode 11 is not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include at least one selected from a holeinjection layer, a hole transport layer, an electron blocking layer, anda buffer layer.

The hole transport region may include only either a hole injection layeror a hole transport layer. In some embodiments, the hole transportregion may have a structure of hole injection layer/hole transport layeror hole injection layer/hole transport layer/electron blocking layer,which are sequentially stacked in this stated order from the firstelectrode 11.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 11 by using, forexample, one or more methods selected from vacuum deposition, spincoating, casting, and Langmuir-Blodgett (LB) deposition.

When a hole injection layer is formed by vacuum deposition, thedeposition conditions may vary according to a material that is used toform the hole injection layer, and the structure and thermalcharacteristics of the hole injection layer. For example, the depositionconditions may include a deposition temperature of about 100 to about500° C., a vacuum pressure of about 10⁻⁸ to about 10⁻³ torr, and adeposition rate of about 0.01 to about 100 Angstroms per second (Å/sec).However, the deposition conditions are not limited thereto.

When the hole injection layer is formed using spin coating, coatingconditions may vary according to the material used to form the holeinjection layer, and the structure and thermal properties of the holeinjection layer. For example, a coating speed may be from about 2,000revolutions per minute (rpm) to about 5,000 rpm, and a temperature atwhich a heat treatment is performed to remove a solvent after coatingmay be from about 80° C. to about 200° C. However, the coatingconditions are not limited thereto.

Conditions for a hole transport layer and an electron blocking layer maybe understood by referring to conditions for forming the hole injectionlayer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

Ar₁₀₁ and Ar₁₀₂ in Formula 201 may be each independently selected from

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, a hydroxyl group, a cyano group,a nitro group, an amino group, an amid no group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₂-C₁₀ heterocycloalkenylgroup, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group.

xa and xb in Formula 201 may be each independently an integer of 0 to 5,or 0, 1 or 2. For example, xa may be 1 and xb may be 0, but xa and xbare not limited thereto.

R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ in Formulae 201 and 202 maybe each independently selected from

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C_(i)-C_(io) alkyl group (for example, a methyl group, an ethyl group,a propyl group, a butyl group, a pentyl group, a hexyl group, and soon), or a C₁-C₁₀ alkoxy group (for example, a methoxy group, an ethoxygroup, a propoxy group, a butoxy group, a pentoxy group, and so on);

a C₁-C₁₀ alkyl group or a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, or a pyrenyl group; or

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group, but they are notlimited thereto.

R₁₀₉ in Formula 201 may be

a phenyl group, a naphthyl group, an anth acenyl group, and a pyridinylgroup; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthracenyl group, and a pyridinyl group.

According to an embodiment, the compound represented by Formula 201 maybe represented by Formula 201A below, but is not limited thereto:

R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ in Formula 201A may be understood byreferring to the description provided herein.

For example, the compound represented by Formula 201 and the compoundrepresented by Formula 202 may include compounds HT1 to HT20 illustratedbelo but are not limited thereto.

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes both a hole injection layer and a holetransport layer, a thickness of the hole injection layer may be in arange of about 100 Å to about 10,000 Å, for example, about 100 Å toabout 1,000 Å, and a thickness of the hole transport layer may be in arange of about 50 Å to about 2,000 Å, for example about 100 Å to about1,500 Å. While not wishing to be bound by theory, it is understood thatwhen the thickness values of the hole transport region, the holeinjection layer, and the hole transport layer are within these ranges,satisfactory hole transporting characteristics may be obtained without asubstantial increase in driving voltage,

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion,

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments are not limitedthereto. Non-limiting examples of the p-dopant are a quinone derivative,such as tetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyanogroup-containing compound, such as Compound HT-D1 or Compound HT-D2below, but are not limited thereto.

The hole transport region may include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distancedepending on a wavelength of light emitted from the emission layer, andthus, the efficiency of a formed organic light-emitting device may beimproved.

Then, an emission layer may be formed on the hole transport region byvacuum deposition, spin coating, casting, LB deposition, or the like.When the emission layer is formed by vacuum deposition or spin coating,the deposition or coating conditions may be similar to those applied toform the hole injection layer although the deposition or coatingconditions may vary according to the material that is used to form theemission layer.

The electron transport region may further include an electron blockinglayer. The electron blocking layer may include, for example, mCP, but amaterial therefor is not limited thereto.

When the organic light-emitting device is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer. Insome embodiments, due to a stack structure including a red emissionlayer, a green emission layer, and/or a blue emission layer, theemission layer may emit white light.

The emission layer may include the condensed cyclic compound representedby Formula 1. The emission layer may include a dopant. The dopant may beat least one selected from a phosphorescent dopant and a fluorescentdopant.

For example, a host in the emission layer may include the condensedcyclic compound represented by Formula 1.

A dopant in the emission layer may be a fluorescent dopant that emitslight according to a fluorescent emission mechanism or a phosphorescentdopant that emits light according to a phosphorescent emissionmechanism.

According to an embodiment, the dopant in the emission layer may be aphosphorescent dopant, and the phosphorescent dopant may include anorganometallic compound represented by Formula 81 below:

In Formula 81,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm);

Y₁ to Y₄ are each independently carbon (C) or nitrogen (N);

Y₁ and Y₂ are linked via a single bond or a double bond, and Y₃ and Y₄are linked via a single bond or a double bond;

CY₁ and CY₂ are each independently selected from a benzene, anaphthalene, a fluorene, a spiro-fluorene, an indene, a pyrrole, athiophene, a furan, an imidazole, a pyrazole, a thiazole, anisothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, apyrimidine, a pyridazine, a quinoline, an isoquinoline, abenzoquinoline, a quinoxaline, a quinazoline, a carbazole, abenzoimidazole, a benzofuran, a benzothiophene, an isobenzothiophene, abenzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole,a triazine, a dibenzofuran, and a dibenzothiophene, and CY₁ and CY₂ areoptionally linked to each other through a single bond or an organiclinking group;

R₈₁ to R₈₂ may be each independently hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, —SF₅, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), or —B(Q₅)(Q₇);

a81 and a82 are each independently an integer of 1 to 5;

n81 is an integer of 0 to 4;

n82 is 1, 2, or 3; and

L₈₁ is a monovalent organic ligand, a divalent organic ligand, or atrivalent organic ligand.

R₈₁ and R₆₂ may be understood by referring to the description providedherein in connection with R₄₁.

The phosphorescent dopant may include at least one selected fromCompounds PD1 to PD78 and Flr6 below, but embodiments are not limitedthereto;

In some embodiments, the phosphorescent dopant may include PtOEP:

When the emission layer includes a host and a dopant, the amount of thedopant may be in a range of about 0.01 to about 20 parts by weight basedon 100 parts by weight of the host, but is not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the emission layer is within this range, excellent light-emissioncharacteristics may be obtained without a substantial increase indriving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer, and an electroninjection layer.

For example, the electron transport region may have a structure of holeblocking layer/electron transport layer/electron injection layer or astructure of electron transport layer/electron injection layer, but thestructure of the electron transport region is not limited thereto. Theelectron transport layer may have a single-layered structure or amulti-layer structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transportlayer, and the electron injection layer which constitute the electrontransport region may be understood by referring to the conditions forforming the hole injection layer.

When the electron transport layer includes a hole blocking layer, thehole blocking layer may include, for example, at least one of BCP andBphen, but may also include other materials.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the hole blocking layer is within these ranges, the hole blockinglayer may have excellent hole blocking characteristics without asubstantial increase in driving voltage.

The electron transport layer may further include, in addition to theorganometallic compound represented by Formula 1, at least one selectedfrom BCP, Bphen, Alq₃, Balq, TAZ, and NTAZ.

In some embodiments, the electron transport layer may include at leastone of ET1 and ET19, but are not limited thereto:

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whilenot wishing to be bound by theory, it is understood that when thethickness of the electron transport layer is within the range describedabove, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

Also, the electron transport layer may further include, in addition tothe materials described above, ametal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2.

The electron transport layer may include an electron injection layerthat promotes flow of electrons from the second electrode 19 thereinto,

The electron injection layer may include at least one selected from,LiF, NaCl, CsF, Li₂O, BaO, and LiQ.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the electron injection layer is within the range described above, theelectron injection layer may have satisfactory electron injectioncharacteristics without a substantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for forming the secondelectrode 19 may be metal, an alloy, an electrically conductivecompound, and a combination thereof, which have a relatively low workfunction. For example, lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) may be formed as the material for forming thesecond electrode 19. To manufacture a top emission-type light-emittingdevice, a transmissive electrode formed using ITO or IZO may be used asthe second electrode 19.

Hereinbefore, the organic light-emitting device has been described withreference to FIG. 1, but is not limited thereto,

A C₁-C₆₀ alkyl group as used herein refers to a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms,Detailed examples thereof are a methyl group, an ethyl group, a propylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, apentyl group, an iso-amyl group, and a hexyl group, A C₁-C₆₀ alkylenegroup as used herein refers to a divalent group having the samestructure as the C₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group as used herein refers to a monovalent grouprepresented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group). Detailedexamples thereof are a methoxy group, an ethoxy group, and anisopropyloxy group.

A C₂-C₆₀ alkenyl group as used herein refers to a hydrocarbon groupformed by placing at least one carbon double bond in the middle or atthe terminal of the C₂-C₆₀ alkyl group. Detailed examples thereof are anethenyl group, a propenyl group, and a butenyl group. A C₂-C₆₀alkenylene group as used herein refers to a divalent group having thesame structure as the C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group as used herein refers to a hydrocarbon grouphaving at least one carbon triple bond in the middle or at the terminalof the C₂-C₆₀ alkyl group. Detailed examples thereof are an ethynylgroup and a propynyl group. A C₂-C₆₀ alkynylene group as used hereinrefers to a divalent group having the same structure as the C₂-C₆₀alkynyl group,

A C₃-C₁₀ cycloalkyl group as used herein refers to a monovalenthydrocarbon monocyclic group having 3 to 10 carbon atoms. Detailedexamples thereof are a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C₃-C₁₀cycloalkylene group as used herein refers to a divalent group having thesame structure as the C₃-C₁₀ cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group as used herein refers to a monovalentmonocyclic group having at least one heteroatom selected from N, O, P,and S as a ring-forming atom and 1 to 10 carbon atoms. Detailed examplesthereof are a tetrahydrofuranyl group and a tetrahydrothiophenyl group.A C₁-C₁₀ heterocycloalkylene group as used herein refers to a divalentgroup having the same structure as the C₁-C₁₀ heterocycioalkyl group.

A C₃-C₁₀ cycloalkenyl group as used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least one doublebond in the ring thereof, and which is not aromatic. Detailed examplesthereof are a cyclopentenyl group, a cyclohexenyl group, and acycloheptenyl group. A C₃-C₁₀ cycloalkenylene group as used hereinrefers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

A C₁-C₁₀ heterocycloalkenyl group as used herein refers to a monovalentmonocyclic group that has at least one heteroatom selected from N, O, P,and S as a ring-forming atom, 1 to 10 carbon atoms, and at least onedouble bond in its ring. Detailed examples of the C₁-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a2,3-dihydrothiophenyl group. A C₁-C₁₀ heterocycloalkenylene group asused herein refers to a divalent group having the same structure as theC₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group as used herein refers to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group as used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Detailedexamples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other.

A C₁-C₆₀ heteroaryl group as used herein refers to a monovalent grouphaving a carbocyclic aromatic system that has at least one heteroatomselected from N, O, P, and S as a ring-forming atom, and 1 to 60 carbonatoms. A C₁-C₆₀ heteroarylene group as used herein refers to a divalentgroup having a carbocyclic aromatic system that has at least oneheteroatom selected from N, O, P, and S as a ring-forming atom, and 1 to60 carbon atoms. Examples of the C₁-C₆₀ heteroaryl group are a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group. Whenthe C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group eachinclude two or more rings, the rings may be fused to each other.

A C₆-C₆₀ aryloxy group as used herein indicates —OA₁₀₂ (wherein A₁₀₂ isthe C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group indicates —SA₁₀₃(wherein A₁₀₃ is the C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group as used hereinrefers to a monovalent group that has two or more rings condensed toeach other, only carbon atoms (for example, the number of carbon atomsmay be in a range of 8 to 60) as a ring-forming atom, and which isnon-aromatic in the entire molecular structure. An example of themonovalent non-aromatic condensed polycyclic group is a fluorenyl group.A divalent non-aromatic condensed polycyclic group as used herein refersto a divalent group having the same structure as the monovalentnon-aromatic condensed polycyclic group.

A monovalent non-aromatic condensed heteropolycyclic group as usedherein refers to a monovalent group that has two or more rings condensedto each other, has a heteroatom selected from N, O, P, and S other thancarbon atoms (for example, the number of carbon atoms may be in a rangeof 1 to 60), as a ring-forming atom, and which is non-aromatic in theentire molecular structure. An example of the monovalent non-aromaticcondensed heteropolycyclic group is a carbazolyl group. A divalentnon-aromatic condensed heteropolycyclic group as used herein refers to adivalent group having the same structure as the monovalent non-aromaticcondensed heteropolycyclic group.

At least one of substituents of the substituted C₃-C₁₀ cycloalkylenegroup, substituted C₁-C₁₀ heterocycloalkylene group, substituted C₃-C₁₀cycloalkenylene group, substituted C₁-C₁₀ heterocycloalkenylene group,substituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, substituted divalent non-aromatic condensed polycyclic group,substituted divalent non-aromatic condensed heteropolycyclic group,substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₃-C₁₀ cycloalkyl group,substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C-₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group asused herein is selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₅-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₃₁)(Q₃₂)(C₃₃),

wherein Q₃₁ to Q₃₃ may be each independently selected from hydrogen, aC₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

The “biphenyl group” as used herein refers to “a phenyl groupsubstituted with a phenyl group.”

Hereinafter, a compound and an organic light-emitting device accordingto embodiments are described in detail with reference to SynthesisExample and Examples. However, the organic light-emitting device is notlimited thereto. The wording “B was used instead of A” used indescribing Synthesis Examples means that an amount of A used wasidentical to an amount of B used, in terms of a molar equivalent.

EXAMPLE Synthesis Example 1 Synthesis of Compound 5

1) Synthesis of Intermediate I-5-1

2-(phenylamino)benzoic acid (2.5 grams (g), 0.12 moles (mol)), thionylchloride (1.39 g, 0.13 mol), and 50 milliliters (mL) of methanol wereadded to a flask, and the mixture was allowed to react for 5 hours. Oncethe reaction was completed, the reaction mixture was filtered, and theremaining solid was washed with water to obtain Intermediate I-3-1 (2.4g, 90%).

2) Synthesis of Intermediate I-5-2

A Grignard reaction was performed by using Intermediate I-3-1 (2 g,0.009 mol) and phenyl magnesium bromide (2.07 g, 0.012 mol) to obtaindiphenyl(2-(phenylamino)phenyl)methanol. Without separatingdiphenyl(2-(phenylamino)phenyl)methanol, 30 mL of sulfuric acid wasadded thereto to obtain Intermediate I-5-2 (1.6 g, 56%).

3) Synthesis of Intermediate I-5-3

1,3-dibromo-5-iodobenzene (20 g, 55.28 millimoles (mmol)),(2-cyanophenyl)boronic acid (9.74 g, 66.33 mmol), potassium carbonate(15.28 g, 110.56 mmol), and 0.05 mole percent (mol %) of Pd catalystwere added to a reaction vessel, and a mixture of tetrahydrofuran anddistilled water (110 mL, 1:1 volume to volume (v/v)) were added thereto.The reaction mixture was allowed to react for 12 hours. Once thereaction was complete, methanol was added thereto to form a precipitate,which was then filtered. The precipitate was purified by columnchromatography to obtain Intermediate I-5-3 (9.1 g, 48%).

4) Synthesis of Intermediate I-5-4

Intermediate I-5-3 (8.5 g, 25.19 mmol), Intermediate I-5-2 (7 g, 21mmol), copper iodide (0.2 g, 1.05 mmol), sodium-tert-butoxide (4.035 g,42 mmol), trans-1,2-diamino cyclohexane (0.48 g, 4.2 mmol), and 50 mL ofdimethylformamide were reacted at a temperature of 150° C. for 12 hours,The reaction mixture was cooled to room temperature, and methanol wasadded thereto to form a precipitate, which was then filtered. Theprecipitate was purified by column chromatography to obtain IntermediateI-5-4 (6.6 g, 45%).

5) Synthesis of Compound 5

9H-carbazole (1 g, 5.98 mmol), Intermediate I-5-4 (4.23 g, 7.18 mmol),copper iodide (0.57 g, 2.99 mmol), potassium carbonate (6.362 g, 46mmol), 1,10-phenanthroline (1.08 g, 5.98 mmol), and 30 mL ofdimethylformamide were reacted for 24 hours, The obtained crude productwas purified by column chromatography using dichloromethane andn-hexane. The obtained purification product was re-crystallized fromethyl acetate and ethanol to obtain Compound 5 (1.1 g, 98%). Compound 5was identified by LC-Mass.

LC-Mass (calc.: 675.83 g/mol, found: M+H=676 g/mol).

Comparative Synthesis Example 1 Synthesis of Compound A

Acridine (10 g, 47.78 mmol), 9-(3-bromophenyl)-9H-carbazole (18.4 g,57.34 mmol), potassium-tert-butoxide (8 g, 71.67 mmol), palladiumacetate (0.536 g, 2.39 mmol), tri-tert-butylphosphine (50 wt % toluene)(0.774 mL, 1.91 mmol), and 60 mL of toluene were reacted at atemperature of 110° C. for 24 hours. Once the reaction was completed,filtering was performed thereon to obtain a crude product. The obtainedcrude product was re-crystallized twice by using toluene and methanol toobtain Compound A (14.6 g, 68%). Compound A was identified by LC-Mass.

LC-Mass (calc.: 450.59 g/mol, found: M+H=451 g/mol).

Comparative Synthesis Example 2 Synthesis of Compound B

9,9-diphenyl-9,10-dihydroacridine (10 g, 30 mmol),9-(3-bromophenyl)-9H-carbazole (11.6 g, 36 mmol), sodium-tert-butoxide(4.324 g, 45 mmol), palladium acetate (0.337 g, 1.5 mmol),tri-tert-butylphosphine (0,6 mL, 1.5 mmol), and 60 mL of toluene werereacted at a temperature of 110° C. for 24 hours. Once the reaction wascompleted, filtering was performed thereon to obtain a crude product.The obtained crude product was re-crystallized twice by usingdichloromethane and n-hexane to obtain Compound B (4.44 g, 26%).Compound B was identified by LC-Mass.

LC-Mass (calc.: 574,73 g/mol, found: M+H=575 g/mol).

Comparative Synthesis Example 3 Synthesis of Compound C

9,9-diphenyl-9,10-dihydroacridine (10 g, 30 mmol), 1,3-dibromobenzene(15.4 g, 66 mmol), sodium-tert-butoxide (4.324 g, 45 mmol), palladiumacetate (0.337 g, 1.5 mmol), tri-tert-butylphosphine (1.2 mL, 3 mmol),and 60 mL of toluene were reacted at a temperature of 110° C. for 24hours. Once the reaction was completed, filtering was performed thereonto obtain a crude product. The obtained crude product was purified bycolumn chromatography to obtain Compound C (11.5 g, 52%). Compound C wasidentified by LC-Mass.

LC-Mass (calc.: 740.95 g/mol, found: M+H=742 g/mol).

Comparative Synthesis Example 4 Synthesis of Compound D

9,9-diphenyl-9,10-dihydroacridine (10 g, 30 mmol),9-(3′-bromo-[1,1′-biphenyl]-3-yl)-9H-carbazole (14.3 g, 36 mmol),sodium-tert-butoxide (4.324 g, 45 mmol), palladium acetate (0.337 g, 1.5mmol), tri-tert-butylphosphine (0.6 mL, 1.5 mmol), and 60 mL of toluenewere reacted at a temperature of 110° C.for 24 hours. Once the reactionwas completed, filtering was performed thereon to obtain a crudeproduct. The obtained crude product was purified by columnchromatography to obtain Compound D (16 g, 84%). Compound D wasidentified by LC-Mass.

LC-Mass (calc.: 650.83 g/mol, found: M+H=652 g/mol).

Evaluation Example 1 Evaluation on HOMO, LUMO, and Triplet (T₁) EnergyLevels

HOMO, LUMO and T₁ energy levels of Compounds 5 and A to D were evaluatedaccording to the method shown in Table 1. Results thereof are shown inTable 2.

TABLE 1 HOMO energy A potential (volts, V)-current (amperes, A) graphlevel of each compound was obtained by using cyclic evaluationvoltammetry (CV) (electrolyte: 0.1 molar (M) method Bu₄NClO₄/solvent:CH₂Cl₂/electrode: 3 electrode system (working electrode: GC, referenceelectrode: Ag/AgCl, auxiliary electrode: Pt)). From reduction onset ofthe graph, a HOMO energy level of the compound was calculated. LUMOenergy Each compound was diluted at a concentration of level 1 × 10⁻⁵ Min CHCl₃, and an UV absorption spectrum evaluation thereof was measuredat room temperature by using method a Shimadzu UV-350 spectrometer, anda LUMO energy level thereof was calculated by using an optical band gap(Eg) from an edge of the absorption spectrum. T1 energy A mixture (eachcompound was dissolved in an level amount of 1 milligram (mg) in 3 cubiccentimeters evaluation (cc) of toluene) of toluene and, each compoundwas method loaded into a quartz cell. The resultant quartz cell wasloaded into liquid nitrogen (77 Kelvin (K)) and a photoluminescencespectrum thereof was measured by using a device for measuringphotoluminescence. The obtained spectrum was compared with aphotoluminescence spectrum measured at room temperature, and peaksobserved only at low temperature were analyzed to calculate T₁ energylevels.

TABLE 2 Compound No. HOMO (eV) LUMO (eV) T₁ (eV) Compound 5 −5.57 −1.983.02 Compound A −5.39 −1.80 3.02 Compound B −5.47 −1.89 3.01 Compound C−5.42 −1.91 3.07 Compound D −5.46 −1.91 3.04

From Table 2, it is seen that Compound 5 above has electriccharacteristics that are suitable for use as a material for forming anorganic light-emitting device.

Evaluation Example 2 Thermal Characteristics Evaluation

Thermal analysis (N₂ atmosphere, temperature range: from roomtemperature to 800° C. (10° C./min)-TGA, from room temperature to 400°C.-DSC, Pan Type: Pt Pan in disposable Al Pan(TGA), and disposable Alpan(DSC)) was performed on Compounds 5, and A to C by using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC),and results thereof are shown in Table 3, As shown in Table 3, it isseen that Compound 5 has excellent thermal stability.

TABLE 3 Tg (° C.) Td (° C., 0.1%) Compound 5 163 375 Compound A — 282Compound B 108 297 Compound C 133 301 Compound D 127 245

Example 1

A glass substrate with a 1,500 Å-thick ITO (Indium tin oxide) electrode(first electrode, anode) formed thereon was washed with distilled waterand ultrasonic waves. When the washing with distilled water wascompleted, sonification washing was performed using a solvent, such asisopropyl alcohol, acetone, or methanol. The result was dried and thentransferred to a plasma washer, and the resultant substrate was washedwith oxygen plasma for 5 minutes and then, transferred to a vacuumdepositing device.

Compound HT3 and Compound HP-D2 were co-deposited on the ITO electrodeon the glass substrate to form a hole injection layer having a thicknessof 100 Angstroms (Å). Then, Compound HT3 was deposited on the holeinjection layer to form a hole transport layer having a thickness of1,300 Å, and mCP was deposited on the hole transport layer to form anelectron blocking layer having a thickness of 150 Å, thereby completingthe manufacture of a hole transport region.

On the hole transport region, Compound 5 (host) and Flr6 (dopant, 10percent by weight (wt %)) were co-deposited to form an emission layerhaving a thickness of 300 Å.

BCP was vacuum-deposited on the emission layer to form a hole blockinglayer having a thickness of 100 Å. Compound ET3 and Liq were vacuumdeposited together on the hole blocking layer to form an electrontransport layer having a thickness of 250 Å. Lig was deposited on theelectron transport layer to form an electron injection layer having athickness of 5 Å, and an Al second electrode (cathode) having athickness of 1,000 Å was formed on the electron injection layer tocomplete manufacturing of an organic light-emitting device.

Comparative Examples 1 to 4

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that in forming an emission layer, for use as ahost, corresponding compounds shown in Table 4 were used instead ofCompound 5.

Evaluation Example 4 Evaluation on Characteristics of OrganicLight-Emitting Devices

The driving voltage, current density, efficiency, power efficiency,quantum efficiency, and lifespan of the organic light-emitting devicesof Example 1 and Comparative Examples 1 to 4 were measured by using acurrent-voltage meter (Keithley 2400) and a luminance meter (MinoltaCs-1000A). The results thereof are shown in Table 4. FIG. 2 is aluminance-efficiency graph of organic light-emitting devicesmanufactured according to Example 1 and Comparative Examples 1 to 4.FIG. 3 is a luminance-external quantum efficiency graph of the organiclight-emitting devices. FIG. 4 shows electroluminescent (EL) spectra ofthe organic light-emitting devices.

TABLE 4 Driving Current Quantum voltage efficiency efficiency Emis-(relative (relative (relative sion Host value) value) value) colorExample 1 Compound 5 109 637 587 blue Comparative Compound A 100 100 100blue Example 1 Comparative Compound B 112 79 81 blue Example 2Comparative Compound C 96 58 56 blue Example 3 Comparative Compound D114 134 100 blue Example 4

From Table 4 and FIGS. 2 to 4 it is seen that the organic light-emittingdevice according to Example 1 has lower driving voltage and higherefficiency than the organic light-emitting devices of ComparativeExamples 1 to 4.

The condensed cyclic based compounds according to embodiments haveexcellent electric characteristics and thermal stability. Accordingly,an organic light-emitting device including the condensed cyclic basedcompounds may have a low driving voltage, high efficiency, high power,high quantum efficiency, and a long lifespan.

It should be understood that exemplary embodiments described hereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each exemplaryembodiment should typically be considered as available for other similarfeatures or aspects in other exemplary embodiments.

While one or more exemplary embodiments have been described withreference to the figures, it will be understood by those of ordinaryskill in the art that various changes in form and details may be madetherein without departing from the spirit and scope as defined by thefollowing claims.

What is claimed is:
 1. A condensed cyclic compound represented byFormula 1:

wherein, in Formula 1, X₁ is N or C(R₁), X₂ is N or C(R₂), X₃ is N orC(R₃), X₄ is N or C(R₄), X₆ is N or C(R₅), X₆ is N or C(R₆), X₇ is N orC(R₇), X₈ is N or C(R₈), X₁₁ is N or C(R₁₁), X₁₂ is N or C(R₁₂), X₁₃ isN or C(R₁₃), X₁₄ is N or C(R₁₄), X₁₅ is N or C(R₁₅), X₁₆ is N or C(R₁₆),X₁₇ is N or C(R₁₇), and X₁₈ is N or C(R₁₈); Y₁₁ is O, S, C(R₁₀₁)(R₁₀₂),or Si(R₁₀₁)(R₁₀₂); Z₁₁ to Z₁₄ are each independently selected from N,C(A₁₁), and C(A₁₂); at least one of Z₁₁ to Z₁₄ is C(A₁₁); A₁₁ comprisesat least one cyano group (CN); and is a cyano group (CN) or a grouprepresented by one of Formulae 2-1 to 2-10; A₁₂ is hydrogen, deuterium,—F, a hydroxyl group, a cyano group (CN), a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, and aC₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group,each substituted with at least one selected from a deuterium, —F, ahydroxyl group, a cyano group (CN), a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof; a phenyl group, a pyridinylgroup, a fluorenyl group, a dibenzofuranyl group, and adibenzothiophenyl group; a phenyl group, a pyridinyl group, a fluorenylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group, eachsubstituted with at least one selected from a deuterium, —F, a hydroxylgroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, apyridinyl group, a fluorenyl group, a dibenzofuranyl group, adibenzothiophenyl group and —Si(Q₂₁)(Q₂₂)(Q₂₃); and —Si(Q₃₁)(Q₃₂)(Q₃₃);

wherein, in Formulae 2-1 to 2-10, X₂₁ is N or C(R₂₁), X₂₂ is N orC(R₂₂), X₂₃ is N or C(R₂₃), X₂₄ is N or C(R₂₄), X₂₅ is N or C(R₂₅), R₁to R₈, R₁₁ to R₁₈, R₁₀₁, R₁₀₂, R₂₁ to R₂₅, and R₂₀₁ to R₂₀₃ are eachindependently selected from hydrogen, deuterium, —F, a hydroxyl group, acyano group (CN), a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substitutedwith at least one selected from a deuterium, —F, a hydroxyl group, acyano group (CN), a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof; a phenyl group, a pyridinyl group, a fluorenylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group; a phenylgroup, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, anda dibenzothiophenyl group, each substituted with at least one selectedfrom a deuterium, —F, a hydroxyl group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, adibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₁)(Q₂)(Q₃);and —Si(Q₁₁)(Q₁₂)(Q₁₃), R₁₀₁ and R₁₀₂ are optionally linked to eachother to form a saturated ring or an unsaturated ring; b201 is selectedfrom 1, 2, 3, 4, and 5; b202 and b203 are each independently selectedfrom 1, 2, 3, and 4; and * indicates a carbon atom in Formula 1, whereinQ₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃ and Q₃₁ to Q₃₃ are each independentlyselected from hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group_(;) a naphthyl group, a pyridinyl group, a fluorenyl group,a dibenzofuranyl group, and a dibenzothiophenyl group.
 2. The condensedcyclic compound of claim 1, wherein X₁ is N, X₂ is C(R₂), X₃ is C(R₃),X₄ is C(R₄), X₅ is C(R₅), X₆ is C(R₆), X₇ is C(R₇), X₈ is C(R₈), X₁₁ isC(R₁₁), X₁₂ is C(R₁₂), X₁₃ is C(R₁₃), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅), X₁₆is C(R₁₆), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₅); X₁ is C(R₁), X₂ is N, X₃ isC(R₃), X₄ is C(R₄), X₅ is C(R₅), X₆ is C(R₆), X₇ is C(R₇), X₈ is C(R₈),X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₃ is C(R₁₃), X₁₄ is C(R₁₄), X₁₅ isC(R₁₅), X₁₆ is C(R₁₆), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈); X₁ is C(R₁), X₂is C(R₂), X₃ is N, X₄ is C(R₄), X₅ is C(R₅), X₆ is C(R₅), X₇ is C(R₇),X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₃ is C(R₁₃), X₁₄ is C(R₁₄),X₁₅ is C(R₁₅), X₁₆ is C(R₁₆), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈); X₁ isC(R₁), X₂ is C(R₂), X₃ is C(R₃), X₄ is N, X₅ is C(R₅), X₆ is C(R₆), X₇is C(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₃ is C(R₁₃), X₁₄is C(R₁₄), X₁₅ is C(R₁₅), X₁₆ is C(R₁₆), X₁₇ is C(R₁₇), and X₁₈ isO(R₁₅); X₁ is C(R₁), X₂ is C(R₂), X₃ is C(R₃), X₄ is C(R₄), X₅ is N, X₆is C(R₆), X₇ is C(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₃ isC(R₁₃), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅), X₁₆ is C(R₁₆), X₁₇ is C(R₁₇), andX₁₈ is C(R₁₈); X₁ is C(R₁), X₂ is C(R₂), X₃ is C(R₃), X₄ is C(R₄), X₅ isC(R₅), X₆ is N, X₇ is C(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂),X₁₃ is C(R₁₃), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅), X₁₆ is C(R₁₆), X₁₇ isC(R₁₇), and X₁₈ is C(R₁₈); X₁ is C(R₁), X₂ is C(R₂), X₃ is C(R₃), X₄ isC(R₄), X₅ is C(R₅), X₆ is C(R₆), X₇ is N, X₈ is C(R₈), X₁₁ is C(R₁₁),X₁₂ is C(R₁₂), X₁₃ is C(R₁₃), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅), X₁₆ isC(R₁₆), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈); X₁ is C(R₁), X₂ is C(R₂), X₃is C(R₃), X₄ is C(R₄), X₅ is C(R₅), X₆ is C(R₆), X₇ is C(R₇), X₈ is N,X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₃ is C(R₁₃), X₁₄ is C(R₁₄), X₁₅ isC(R₁₅), X₁₆ is C(R₁₆), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈); or X₁ is C(R₁),X₂ is C(R₂), X₃ is C(R₃), X₄ is C(R₄), X₅ is C(R₅), X₆ is C(R₆), X₇ isC(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₃ is C(R₁₃), X₁₄ isC(R₁₄), X₁₅ is C(R₁₅), X₁₆ is C(R₁₆), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈).3. The condensed cyclic compound of claim 1, wherein A₁₁ is a cyanogroup (CN) or a group represented by one of Formulae 2-1 to 2-7.
 4. Thecondensed cyclic compound of claim 1, wherein A₁₁ is a cyano group (CN)or a group represented by one of Formulae 3-1 to 3-110:

wherein, in Formulae 3-1 to 3-110, * indicates a carbon atom in Formula1; and X₂₁ to X₂₅, R₂₀₂, R₂₀₃, b201 and b202 are the same as in Formulae2-1 to 2-10.
 5. The condensed cyclic compound of claim 1, wherein A₁₁ isa cyano group (ON) or a group represented by one of Formulae 4-1 to4-110:

wherein, in Formulae 4-1 to 4-110; * indicates a carbon atom in Formula1; and R₂₀₂, R₂₀₃, b201 and b202 are the same as in Formulae 2-1 to2-10.
 6. The condensed cyclic compound of claim 1, wherein A₁₂ ishydrogen, deuterium, —F, a hydroxyl group, a cyano group (CN), a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, and a C₁-C₂₀ alkoxy group; a phenyl group, a pyridinylgroup, a fluorenyl group, a dibenzofuranyl group, and adibenzothiophenyl group; and —Si(Q₃₁)(Q₃₂)(Q₃₃), wherein Q₃₁ to Q₃₃ areeach independently selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a phenyl group, a naphthyl group, and a pyridinyl group.
 7. Thecondensed cyclic compound of claim 1, wherein R₁ to R₈, R₁₁ to R₁₈,R₁₀₁, R₁₀₂, R₂₁ to R₂₅, and R₂₀₁ to R₂₀₃ are each independently selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a methyl group, an ethyl group, an n-propyl group, an isopropylgroup, an n-butyl group, an isobutyl group, a sec-butyl group, atert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentylgroup, a tert-pentyl group, an n-hexyl group, an isohexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, anisooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group,an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decylgroup, an isodecyl group, a sec-decyl group, a tert-decyl group, amethoxy group, an ethoxy group, a propoxy group, a butoxy group, apentoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group; a methyl group, anethyl group, an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a sec-pentyl group, a tert-pentyl group, ann-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group,an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptylgroup, an n-octyl group, an isooctyl group, a sec-octyl group, atert-octyl group, an n-nonyl group, an isononyl group, a sec-nonylgroup, a tert-nonyl group, an n-decyl group, an isodecyl group, asec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, apropoxy group, a butoxy group, a pentoxy group, a phenyl group, apyridinyl group, a fluorenyl group, a dibenzofu anyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof; and —Si(Q₁₁)(Q₁₂)(Q₁₃), wherein Q₁₁ to Q₁₃ are eachindependently selected from hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, afluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.8. The condensed cyclic compound of claim 1, wherein R₁ to R₈, R₁₁ toR₁₈, R₂₁ to R₂₅, and R₂₀₁ to R₂₀₃ are each independently selected fromhydrogen, deuterium, a cyano group, a methyl group, an ethyl group, ann-propyl group, an isopropyl group, an n-butyl group, an isobutyl group,a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentylgroup, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, anisohexyl group, a sec-hexyl group, a tert-hexyl group, and—Si(Q₁₁)(Q₁₂)(Q₁₃), wherein Q₁₁ to Q₁₃ are each independently selectedfrom hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, and a phenylgroup.
 9. The condensed cyclic compound of claim 1, wherein R₁₀₁ andR₁₀₂ are linked to each other to from a structure represented by Formula8:

wherein, in Formula 8, * indicates a carbon atom belonging to Y₁₁ inFormula 1, X₈₁ is N or C(R₈₁), X₈₂ is N or C(R₈₂), X₈₃ is N or C(R₈₃),X₈₄ is N or C(R₈₄), X₈₅ is N or C(R₈₅), X₈₆ is N or C(R₈₆), X₈₇ is N orC(R₈₇), and X₈₈ is N or C(R₈₈), and R₈₁ to R₈₈ are each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, aphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group,a pyrazinyl group, a pyridazinyl group, a triazinyl group, and—Si(Q₃₁)(Q₃₂)(Q₃₃), wherein Q₃₁ to Q₃₃ are each independently hydrogen,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, and a triazinyl group.
 10. The condensed cycliccompound of claim 1, wherein at least one of X₃, X₆, X₁₃, and X₁₆ isC(CN).
 11. The condensed cyclic compound of claim 1, wherein thecondensed cyclic compound represented by Formula 1 is represented by oneof Formulae 1-1 and 1-2:

wherein, in Formulae 1-1 and 1-2, descriptions of X₁ to X₈, X₁₁ to X₁₈,Y₁₁, and A₁₁ are the same as provided in connection with Formula 1; anddescriptions of A_(12a), A_(12b), and A_(12c) are the same as providedin connection with A₁₂ in Formula
 1. 12. The condensed cyclic compoundof claim 1, wherein the condensed cyclic compound represented by Formula1 is represented by one of Formulae 1-3 to 1-6:

wherein, in Formulae 1-3 to 1-6, descriptions of X₁ to X₈, X₁₁ to X₁₈,Y₁₁, R₁₀₁, R₁₀₂, and A₁₁ are the same as provided in connection withFormula 1; A_(12a), A_(12b), and A_(12c) are the same as provided inconnection with A₁₂ in Formula 1; and R₈₁ to R₈₈ are each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group_(;)a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and—Si(Q₃₁)(Q₃₂)(Q₃₃), wherein Q₃₁ to Q₃₃ are each independently hydrogen,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyi group, and a triazinyl group.
 13. The condensed cycliccompound of claim 1, wherein the condensed cyclic compound representedby Formula 1 is represented by one of Formulae 1-11 to 1-25:

wherein, in Formulae 1-11 to 1-25, X₁, X₂, X₄, X₅, X₇, X₈, X₁₁, X₁₂,X₁₄, X₁₅, X₁₇, X₁₈, Y₁₁, and Z₁₁ to Z₁₄ are the same as in Formula 1.14. The condensed cyclic compound of claim 13, wherein the condensedcyclic compound represented by Formula 1 is represented by one ofFormulae 1-11 to 1-25; and X₁ is N, X₂ is C(R₂), X₄ is C(R₄), X₅ isC(R₅), X₇ is C(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₄ isC(R₁₄), X₁₅ is C(R₁₅), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈); X₁ is C(R₁), X₂is N, X₄ is C(R₄), X₅ is C(R₅), X₇ is C(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁),X₁₂ is C(R₁₂), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅), X₁₇ is C(R₁₇), and X₁₈ isC(R₁₈); X₁ is C(R_(I)), X₂ is C(R₂), X₄ is N, X₅ is C(R₅), X₇ is C(R₇),X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅),X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈); X₁ is C(R₁), X₂ is C(R₂), X₄ is C(R₄),X₅ is N, X₇ is C(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₄ isC(R₁₄), X₁₅ is C(R₁₅), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈); X₁ is C(R₁), X₂is C(R₂), X₄ is C(R₄), X₅ is C(R₅), X₇ is N, X₈ is C(R₈), X₁₁ is C(R₁₁),X₁₂ is C(R₁₂), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅), X₁₇ is C(R₁₇), and X₁₈ isC(R₁₈); or X₁ is C(R₁), X₂ is C(R₂), X₄ is C(R₄), X₅ is C(R₅), X₇ isC(R₇), X₈ is N, X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₄ is C(R₁₄), X₁₅ isC(R₁₅), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈).
 15. The condensed cycliccompound of claim 1, wherein the condensed cyclic compound representedby Formula 1 is represented by one of Formulae 1-31 to 1-45:

wherein, in Formulae 1-31 to 1-45, X₁, X₂, X₄, X₅, X₇, X₈, X₁₁, X₁₂,X₁₄, X₁₅, X₁₇, X₁₈, and Z₁₁ to Z₁₄ are the same as in Formula 1; and R₈₁to R₈₈ are each independently selected from hydrogen, deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group_(;) acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), wherein Q₃₁ to Q₃₃ areeach independently selected from hydrogen, a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, anda triazinyl group.
 16. The condensed cyclic compound of claim 15,wherein the condensed cyclic compound represented by Formula 1 isrepresented by one of Formulae 1-31 to 1-45; and X₁ is N, X₂ is C(R₂),X₄ is C(R₄), X₅ is C(R₅), X₇ is C(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂is C(R₁₂), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅), X₁₇ is C(R₁₇), and X₁₈ isC(R₁₈); X₁ is C(R₁), X₂ is N, X₄ is C(R₄), X₅ is C(R₅), X₇ is C(R₇), X₈is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅),X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈): X₁ is C(R₁), X₂ is C(R₂), X₄ is N, X₅is C(R₅), X₇ is C(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₄ isC(R₁₄), X₁₅ is C(R₁₅), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈); X₁ is C(R₁), X₂is C(R₂), X₄ is C(R₄), X₅ is N, X₇ is C(R₇), X₈ is C(R₈), X₁₁ is C(R₁₁),X₁₂ is C(R₁₂), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅), X₁₇ is C(R₁₇), and X₁₈ isC(R₁₈); X₁ is C(R₁), X₂ is C(R₂), X₄ is C(R₄), X₅ is C(R₅), X₇ is N, X₈is C(R₈), X₁₁ is C(R₁₁), X₁₂ is C(R₁₂), X₁₄ is C(R₁₄), X₁₅ is C(R₁₅),X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈); or X₁ is C(R₁), X₂ is C(R₂), X₄ isC(R₄), X₅ is C(R₅), X₇ is C(R₇), X₈ is N, X₁₁ is C(R₁₁), X₁₂ is C(R₁₂),X₁₄ is C(R₁₄), X₁₅ is C(R₁₅), X₁₇ is C(R₁₇), and X₁₈ is C(R₁₈).
 17. Thecondensed cyclic compound of claim 1, wherein the condensed cycliccompound represented by Formula 1 is selected from Compounds 1 to 134:


18. An organic light-emitting device comprising: a first electrode; asecond electrode; and an organic layer disposed between the firstelectrode and the second electrode, wherein the organic layer comprisesan emission layer and at least one condensed cyclic compound representedby Formula 1 of claim
 1. 19. The organic light-emitting device of claim18, wherein the emission layer comprises the at least one condensedcyclic compound.
 20. The organic light-emitting device of claim 19,wherein the emission layer further comprises a phosphorescent dopant.